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Phenylpropanoids, Aromatic Polyketides

 Both phenylpropanoids and aromatic polyketides are natural organic compounds of plant origin biosynthesized via the shikimic acid pathway. Phenylalanine and tyrosine are their precursors.1) Phenylpropanoids are classified in the group of compounds in which side chains with three carbons are attached to a benzene ring. They are ingredients of essential oils obtained from anis, cinnamon bark, and clove and are used for fragrances and aromatherapy.
 Aromatic polyketides are designated as compounds in which carbon chains are extended with malonyl-CoA onto phenylpropanoids.2) Diarylheptanoids are biosynthesized from two cinnamyl-CoA units and one malonyl-CoA. Their two aromatic rings are connected with an aliphatic seven-carbon chain. Stilbenoids, chalconoids, flavonoids and isoflavonoids are formed from a cinnamyl-CoA with three malonyl-CoA units. Chalconoids, flavonoids and isoflavonoids possess a C6-C3-C6 skeleton whereas stilbenoids have a C6-C2-C6 skeleton which arises by decarboxylation during the biosynthesis. Most of them have phenolic hydroxy groups and show antioxidative activity. Some of them show physiologic activities towards plants, such as phytoalexins, with the budding of seeds and adjusting of growth. Isoflavonoids are a unique compound group: they are biosynthesized via the phenyl group migration from flavonoids.2) To date, they are found only in the Leguminosae/Fabacaeae plant family. This distinct biosynthesis triggered researchers to investigate detailed biosynthetic mechanisms.

Fig.1 Structures of Phenylpropanoids and Aromatic Polyketides

■Solubility
They are generally soluble in many organic solvents. They can be rather diffi cult to dissolve in non-polar solvents such as hexane but dissolve well in high polar solvents such as chloroform, methanol and DMSO. Compounds with carboxyl or phenolic hydroxy groups are soluble in aqueous alkaline solutions. Since they are easily oxidized in the liquid state, we suggest you to use them within a short period of time after preparation.

■Storage
Precautions  As long as no special remark is mentioned in the catalogues or labels, they can be stored at room temperature. Solids can be stored longer than liquid compounds or solutions. Note should be taken that compounds with phenolic hydroxy groups are labile to oxidation and can gradually change color from brown to black while being stored. Compounds with aldehyde groups are also apt to be oxidized to carboxylic acids. After unsealing these labile reagents, they should be stored refrigerated or frozen under an inert gas such as nitrogen/argon.

Cinnamic Acids, Cinnamate Esters

A0691
(E)-4-Aminocinnamic Acid
A2413
2-Acetoxycinnamic Acid
C0002
Caffeic Acid
C0181
Chlorogenic Acid Hydrate
C0353
trans-Cinnamic Acid
C0358
Benzyl Cinnamate
C0359
Ethyl (E)-Cinnamate
C0360
Methyl Cinnamate
C0393
trans-p-Coumaric Acid
C0394
trans-o-Coumaric Acid
C0447
α-Cyanocinnamic Acid
C0448
Ethyl α-Cyanocinnamate
C0617
Cholesterol trans-Cinnamate
C0655
trans-m-Coumaric Acid
C0899
Vinyl Cinnamate (stabilized with MEHQ)
C0960
Cinnamyl Cinnamate
C1768
α-CHCA
C1779
Isopropyl Cinnamate
C2677
α-Cyano-3-hydroxycinnamic Acid
D1728
3,4-Dimethoxycinnamic Acid
D1765
Sinapinic Acid
D1972
2,5-Dimethoxycinnamic Acid
D2326
trans-2,3-Dimethoxycinnamic Acid
D2364
2,4-Dimethoxycinnamic Acid
D3794
trans-2,5-Dichlorocinnamic Acid
D4048
2,6-Dichlorocinnamic Acid
E0677
Ethyl (E)-4-Cyanocinnamate
E0739
Ethyl 4-Hydroxy-3-methoxycinnamate
E0856
4-Ethoxycinnamic Acid
H0267
trans-Ferulic Acid
H0524
3-Hydroxy-4-methoxycinnamic Acid
I0815
Isoamyl 4-Methoxycinnamate
M0444
3-Methoxycinnamic Acid
M0449
trans-2-Methoxycinnamic Acid
M0576
trans-4-Methoxycinnamic Acid
M0634
3,4-Methylenedioxycinnamic Acid
M0715
4-Methylcinnamic Acid
M0761
cis-2-Methoxycinnamic Acid
M1082
2-Ethylhexyl 4-Methoxycinnamate
M1204
Ethyl 4-Methoxycinnamate
M1295
2-Methylcinnamic Acid
M1298
3-Methylcinnamic Acid
M1336
(E)-α-Methylcinnamic Acid
M2259
Methyl trans-p-Coumarate
M2519
Methyl Caffeate
M2520
Methyl 2,5-Dihydroxycinnamate
O0172
γ-Oryzanol
P1898
(E)-4-Propoxycinnamic Acid
P2007
2-Phenylethyl (E)-Cinnamate
P2088
Phenethyl Caffeate
T1104
(E)-3,4,5-Trimethoxycinnamic Acid
T1323
Sodium 3,4,5-Trimethoxycinnamate
T1393
2,4,5-Trimethoxycinnamic Acid
T2016
2,3,4-Trimethoxycinnamic Acid
V0153
Verbascoside

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Cinnamaldehydes

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Cinnamic Acid Derivatives

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Phenylpropenes

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Coumarins

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Lignins, Lignans

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Diarylheptanoids

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Stilbenoids

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Chalconoids

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Flavonoids

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Isoflavonoids

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Xanthonoids

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References

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